- A phosphine-free iron complex-catalyzed synthesis of cycloalkanes: Via the borrowing hydrogen strategy
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Herein we report a diaminocyclopentadienone iron tricarbonyl complex catalyzed synthesis of substituted cyclopentane, cyclohexane and cycloheptane compounds using the borrowing hydrogen strategy in the presence of various substituted primary and secondary 1,n diols as alkylating reagents. Deuterium labeling experiments confirm that the diols were the hydride source in this cascade process. This journal is
- Bettoni, Léo,Gaillard, Sylvain,Renaud, Jean-Luc
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p. 12909 - 12912
(2020/11/07)
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- Stereoselective synthesis of alicyclic ketones: A hydrogen borrowing approach
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A highly diastereoselective annulation strategy for the synthesis of alicyclic ketones from diols and pentamethylacetophenone is described. This process is mediated by a commercially available iridium(III) catalyst, and provides efficient access to a wide range of cyclopentane and cyclohexane products with high levels of stereoselectivity. The origins of diastereoselectivity in the annulation reaction have been explored by a series of control experiments, which provides an explanation for how each stereocentre around the newly forged ring is controlled.
- Armstrong, Roly J.,Akhtar, Wasim M.,Frost, James R.,Christensen, Kirsten E.,Stevenson, Neil G.,Donohoe, Timothy J.
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supporting information
(2019/11/13)
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- Direct Synthesis of Cycloalkanes from Diols and Secondary Alcohols or Ketones Using a Homogeneous Manganese Catalyst
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A method for the synthesis of substituted cycloalkanes was developed using diols and secondary alcohols or ketones via a cascade hydrogen borrowing sequence. A non-noble and air-stable manganese catalyst (2 mol %) was used to perform this transformation. Various substituted 1,5-pentanediols (3-4 equiv) and substituted secondary alcohols (1 equiv) were investigated to prepare a collection of substituted cyclohexanes in a diastereoselective fashion. Similarly, cyclopentane, cyclohexane, and cycloheptane rings were constructed from substituted 1,4-butanediol, 1,5-pentanediol, and 1,6-hexanediol, and sterically hindered ketones following a (4 + 1), (5 + 1), and (6 + 1) strategy, respectively. This reaction provides an atom economic methodology to construct two C-C bonds at a single carbon center generating high-value cycloalkanes from readily available alcohols as feedstock using an earth-abundant metal catalyst.
- Kaithal, Akash,Gracia, Lisa-Lou,Camp, Clément,Quadrelli, Elsje Alessandra,Leitner, Walter
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supporting information
(2019/11/21)
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- Stereoselective Synthesis of Cyclohexanes via an Iridium Catalyzed (5 + 1) Annulation Strategy
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An iridium catalyzed method for the synthesis of functionalized cyclohexanes from methyl ketones and 1,5-diols is described. This process operates by two sequential hydrogen borrowing reactions, providing direct access to multisubstituted cyclic products with high levels of stereocontrol. This methodology represents a novel (5 + 1) strategy for the stereoselective construction of the cyclohexane core.
- Akhtar, Wasim M.,Armstrong, Roly J.,Frost, James R.,Stevenson, Neil G.,Donohoe, Timothy J.
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supporting information
p. 11916 - 11920
(2018/09/27)
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- N-[3-(2-CARBOXYETHYL)PHENYL]PIPERIDIN-1-YLACETAMIDE DERIVATIVES AND USE THEREOF AS ACTIVATORS OF SOLUBLE GUANYLATE CYCLASE
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The present application relates to novel substituted 2-(piperidin-1-yl)acetamide derivatives, to processes for preparation thereof, to the use thereof for treatment and/or prevention of diseases, and to the use thereof for production of medicaments for treatment and/or prevention of diseases, especially for treatment and/or prevention of cardiovascular diseases.
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Paragraph 0605-0608
(2015/06/10)
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- Aerobic oxidative desymmetrization of meso-diols with bifunctional amidoiridium catalysts bearing chiral N-sulfonyldiamine ligands
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Asymmetric aerobic oxidation of a range of meso- and prochiral diols with chiral bifunctional Ir catalysts is described. A high level of chiral discrimination ability of Cpa? -Ir complexes derived from (S,S)-1,2-diphenylethylenediamine was successfully demonstrated by desymmetrization of secondary benzylic diols such as cis-indan-1,3-diol and cis-1,4-diphenylbutane-1,4-diol, providing the corresponding (R)-hydroxyl ketones with excellent chemo- and enantioselectivities. Enantiotopic group discrimination in oxidation of symmetrical primary 1,4- and 1,5-diols gave rise to chiral lactones with moderate ees under similar aerobic conditions.
- Moritani, Junki,Hasegawa, Yasuharu,Kayaki, Yoshihito,Ikariya, Takao
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p. 1188 - 1191
(2014/02/14)
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- Aerobic lactonization of diols by biomimetic oxidation
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Coming up for air: Highly efficient aerobic lactonization can be carried out by a biomimetic oxidation system based on coupled redox catalysts (ruthenium catalyst and electron transfer mediators). This system leads to a low-energy electron transfer from diol to molecular oxygen. Various diols were aerobically oxidized to the corresponding five- to nine-membered lactones in good to high yields under mild reaction conditions (see scheme).
- Endo, Yoshinori,Baeckvall, Jan-E.
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supporting information; experimental part
p. 12596 - 12601
(2011/12/03)
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- Complementary lipase-mediated desymmetrization processes of 3-Aryl-1,5-disubstituted fragments. enantiopure synthetic valuable carboxylic acid derivatives
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Desymmetrizaton enzymatic processes have been extensively studied searching for optimal methods of producing enantioenriched monoacetates from prochiral diols and diesters. AK lipase has been found as an excellent biocatalyst for the desymmetriaztion of a series of previously synthesized 3-arylpentane-1,5-diols derivatives. The access to (S)- or (R)-monoacetates in high optical purity (86-99% ee) has been possible by using acetylation or hydrolysis reactions, respectively, where the reaction parameters have been optimized in terms of source and amount of biocatalyst, temperature, solvent, and reaction time. The synthetic potential of enantiopure monoesters has been demonstrated by using these interesting chiral building blocks for the preparation of novel enantiopure carboxylic acid derivatives.
- Rios-Lombardia, Nicolas,Gotor-Fernandez, Vicente,Gotor, Vicente
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p. 811 - 819
(2011/04/23)
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- Stereochemistry of base-induced cleavage of methoxide ion on cis- and trans-1,4-diphenylphosphorinanium salts. A different behavior with a phenyl substituent
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The synthesis and characterization of pure cis- and trans-1,4-diphenyl-1- methoxy-phosphorinanium tetrafluoroborate salts 11a and 11b, molecules designed to evaluate the effect of a phenyl substituent at C-4 on the stereochemical course of base-induced nu
- López-Cortina, Susana,Medina-Arreguin, Araceli,Hernández-Fernández, Eugenio,Berns, Sylvain,Guerrero-Alvarez, Jorge,Ordo?ez, Mario,Fernández-Zertuche, Mario
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experimental part
p. 6188 - 6194
(2010/09/11)
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- ANGIOTENSIN II RECEPTOR ANTAGONISTS
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A compound having the structure (I) wherein R is an angiotensin receptor antagonist active group, Y is selected from the group consisting of (II), and 2) -C(R1H)OC(O)X((CR12R13)-(CHR10)m-(CH2)n-Zp-(CH
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Page/Page column 32
(2009/09/05)
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- NOVEL PIPERIDINE DERIVATIVE
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The invention provides a compound of the following formula (1): wherein m, n, and p are independently an integer of 0 - 4, provided 3 ≤ m + n ≤ 8; X is nitrogen atom or a group of the formula: C-R15; Y is a substituted or unsubstituted aromatic group, etc.; R15, R1, R2, R3, R4 , R5, R6 and R7 are hydrogen atom, a substituted or unsubstituted alkyl group, etc.; and Z is hydrogen atom, cyano group, etc., or a prodrug thereof, or a pharmaceutically acceptable salt thereof, which exhibits an action for enhancing LDL receptor expression, and is useful as a medicament for treating hyperlipidemia, atherosclerosis, etc.
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Page/Page column 40
(2008/06/13)
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- Design, synthesis, and antipicornavirus activity of 1-[5-(4-arylphenoxy) alkyl]-3-pyridin-4-ylimidazolidin-2-one derivatives
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A series of pyridylimidazolidinone derivatives was synthesized and tested in vitro against enterovirus 71 (EV71). On the basis of compound 33 (DBPR103), introduction of a methyl group at the 2- or 3-position of the linker between the imidazolidinone and the biphenyl resulted in markedly improved antiviral activity toward EV71 with IC50 values of 5.0 nM (24b) and 9.3 nM (14a), respectively. Increasing the branched chain to propyl resulted in a progressive decrease in activity, while inserting different heteroatoms entirely rendered the compound only weakly active. The introduction of a bulky group (cyclohexyl, phenyl, or benzyl) led to loss of activity against EV71. The 4-chlorophenyl moiety in 14a was replaced with bioisosteric groups such as oxadiazole (28a-d) or tetrazole (32a,b), dramatically improving anti-EV71 activity and selectivity indices. Compounds 14a, 24b, 28b, 28d, and 32a exhibited a strong activity against lethal EV71, and no apparent cellular toxicity was observed. Three of the more potent imidazolidinone compounds, 14a, 28b, and 32b, were subjected to a large group of picornaviruses to determine their spectrum of antiviral activity.
- Chang, Chih-Shiang,Lin, Ying-Ting,Shih, Shin-Ru,Lee, Chung-Chi,Lee, Yen-Chun,Tai, Chia-Liang,Tseng, Sung-Nien,Chern, Jyh-Haur
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p. 3522 - 3535
(2007/10/03)
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- Fused imidazopyridine derivatives as antihyperlipidemic agents
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A novel compound of the formula: wherein ring Q is an optionally substituted pyridine ring; One of R0, R1and R2is —Y0—Z0, and the other tow groups are a hydrogen, a halogen, an optionally substituted hydroxy group, a hydrocarbon group that may be an optionally substituted hydrocarbon group or an acyl group; Y0is a bond or an optionally substituted bivalent hydrocarbon group; Z0is a basic group which may be bonded via oxygen, nitrogen, —CO—, —CS—, —SO2N(R3)— (where R3is hydrogen or an optionally substituted hydrocarbon group), or S(O)n(wherein n is to 0, 1 or 2); .........is a single bond or a double bond, or a salt thereof, which has an excellent LDL receptor up-regulating, blood-lipids lowering, blood-sugar lowering and diabetic complication-ameliorating activity.
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